TW215055B - - Google Patents

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Publication number: TW215055B
Authority: TW; Taiwan
Prior art keywords: benzyl; phenyl; methyl; methoxyphenyl; patent application
Prior art date: 1990-07-02

Application number

TW080105466A

Other languages

English (en)

Chinese (zh)

Original Assignee

Vertex Pharma

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-07-02

Filing date

1991-07-15

Publication date

1993-10-21

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24186237&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=TW215055(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1991-07-15 Application filed by Vertex Pharma filed Critical Vertex Pharma

1993-10-21 Application granted granted Critical

1993-10-21 Publication of TW215055B publication Critical patent/TW215055B/zh

Links

150000001875 compounds Chemical class 0.000 claims abstract description 95
230000001506 immunosuppresive effect Effects 0.000 claims abstract description 29
230000000694 effects Effects 0.000 claims abstract description 22
102000018679 Tacrolimus Binding Proteins Human genes 0.000 claims abstract description 17
108010027179 Tacrolimus Binding Proteins Proteins 0.000 claims abstract description 16
239000003018 immunosuppressive agent Substances 0.000 claims abstract description 13
210000000056 organ Anatomy 0.000 claims abstract description 11
108090000623 proteins and genes Proteins 0.000 claims abstract description 9
102000004169 proteins and genes Human genes 0.000 claims abstract description 8
206010052779 Transplant rejections Diseases 0.000 claims abstract description 5
241000124008 Mammalia Species 0.000 claims abstract description 4
-1 2-indolyl Chemical group 0.000 claims description 248
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 47
238000011049 filling Methods 0.000 claims description 43
239000000203 mixture Substances 0.000 claims description 33
125000000217 alkyl group Chemical group 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 12
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
229910052786 argon Inorganic materials 0.000 claims description 9
239000007789 gas Substances 0.000 claims description 9
230000002401 inhibitory effect Effects 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 7
206010062016 Immunosuppression Diseases 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims description 6
238000007639 printing Methods 0.000 claims description 6
230000001363 autoimmune Effects 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 5
229910052705 radium Inorganic materials 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
230000028993 immune response Effects 0.000 claims description 4
229940125721 immunosuppressive agent Drugs 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 3
238000012856 packing Methods 0.000 claims description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
229910052692 Dysprosium Inorganic materials 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000001151 peptidyl group Chemical group 0.000 claims description 2
230000001629 suppression Effects 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
ZONYXWQDUYMKFB-UHFFFAOYSA-N flavanone Chemical compound O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 claims 6
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 5
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical group [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 claims 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
125000001041 indolyl group Chemical group 0.000 claims 3
125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 claims 2
241000283973 Oryctolagus cuniculus Species 0.000 claims 2
125000002541 furyl group Chemical group 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
125000006178 methyl benzyl group Chemical group 0.000 claims 2
125000004076 pyridyl group Chemical group 0.000 claims 2
229920002554 vinyl polymer Polymers 0.000 claims 2
125000003163 2-(2-naphthyl)ethyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(C([H])=C([H])C2=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000006483 4-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1I)C([H])([H])* 0.000 claims 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
240000008564 Boehmeria nivea Species 0.000 claims 1
240000006162 Chenopodium quinoa Species 0.000 claims 1
241000270722 Crocodylidae Species 0.000 claims 1
241000252234 Hypophthalmichthys nobilis Species 0.000 claims 1
229910052769 Ytterbium Inorganic materials 0.000 claims 1
150000001336 alkenes Chemical class 0.000 claims 1
125000004946 alkenylalkyl group Chemical group 0.000 claims 1
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
239000001273 butane Substances 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
125000006182 dimethyl benzyl group Chemical group 0.000 claims 1
125000001207 fluorophenyl group Chemical group 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
125000002346 iodo group Chemical group I* 0.000 claims 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
238000004898 kneading Methods 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000006502 nitrobenzyl group Chemical group 0.000 claims 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
125000006187 phenyl benzyl group Chemical group 0.000 claims 1
125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 claims 1
125000004344 phenylpropyl group Chemical group 0.000 claims 1
238000004321 preservation Methods 0.000 claims 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
210000004761 scalp Anatomy 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 claims 1
125000001544 thienyl group Chemical group 0.000 claims 1
125000003944 tolyl group Chemical group 0.000 claims 1
125000001701 trimethoxybenzyl group Chemical group 0.000 claims 1
ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 claims 1
210000004885 white matter Anatomy 0.000 claims 1
NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims 1
208000023275 Autoimmune disease Diseases 0.000 abstract description 12
238000002054 transplantation Methods 0.000 abstract description 9
238000011282 treatment Methods 0.000 abstract description 9
229940124589 immunosuppressive drug Drugs 0.000 abstract description 3
230000006044 T cell activation Effects 0.000 abstract description 2
102000003813 Cis-trans-isomerases Human genes 0.000 abstract 1
108090000175 Cis-trans-isomerases Proteins 0.000 abstract 1
101710103508 FK506-binding protein Proteins 0.000 abstract 1
101710104425 FK506-binding protein 2 Proteins 0.000 abstract 1
101710104423 FK506-binding protein 3 Proteins 0.000 abstract 1
101710104333 FK506-binding protein 4 Proteins 0.000 abstract 1
101710104342 FK506-binding protein 5 Proteins 0.000 abstract 1
101710149710 FKBP-type 16 kDa peptidyl-prolyl cis-trans isomerase Proteins 0.000 abstract 1
101710121306 FKBP-type 22 kDa peptidyl-prolyl cis-trans isomerase Proteins 0.000 abstract 1
101710180800 FKBP-type peptidyl-prolyl cis-trans isomerase FkpA Proteins 0.000 abstract 1
101710104030 Long-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 abstract 1
101710114693 Outer membrane protein MIP Proteins 0.000 abstract 1
101710116692 Peptidyl-prolyl cis-trans isomerase Proteins 0.000 abstract 1
101710111764 Peptidyl-prolyl cis-trans isomerase FKBP10 Proteins 0.000 abstract 1
101710111749 Peptidyl-prolyl cis-trans isomerase FKBP11 Proteins 0.000 abstract 1
101710111747 Peptidyl-prolyl cis-trans isomerase FKBP12 Proteins 0.000 abstract 1
101710111757 Peptidyl-prolyl cis-trans isomerase FKBP14 Proteins 0.000 abstract 1
101710111682 Peptidyl-prolyl cis-trans isomerase FKBP1A Proteins 0.000 abstract 1
101710111689 Peptidyl-prolyl cis-trans isomerase FKBP1B Proteins 0.000 abstract 1
101710147154 Peptidyl-prolyl cis-trans isomerase FKBP2 Proteins 0.000 abstract 1
101710147149 Peptidyl-prolyl cis-trans isomerase FKBP3 Proteins 0.000 abstract 1
101710147152 Peptidyl-prolyl cis-trans isomerase FKBP4 Proteins 0.000 abstract 1
102100020739 Peptidyl-prolyl cis-trans isomerase FKBP4 Human genes 0.000 abstract 1
101710147150 Peptidyl-prolyl cis-trans isomerase FKBP5 Proteins 0.000 abstract 1
101710147138 Peptidyl-prolyl cis-trans isomerase FKBP7 Proteins 0.000 abstract 1
101710147137 Peptidyl-prolyl cis-trans isomerase FKBP8 Proteins 0.000 abstract 1
101710147136 Peptidyl-prolyl cis-trans isomerase FKBP9 Proteins 0.000 abstract 1
101710174853 Peptidyl-prolyl cis-trans isomerase Mip Proteins 0.000 abstract 1
101710200991 Peptidyl-prolyl cis-trans isomerase, rhodopsin-specific isozyme Proteins 0.000 abstract 1
101710092145 Peptidyl-prolyl cis-trans isomerase-like 1 Proteins 0.000 abstract 1
101710092146 Peptidyl-prolyl cis-trans isomerase-like 2 Proteins 0.000 abstract 1
101710092148 Peptidyl-prolyl cis-trans isomerase-like 3 Proteins 0.000 abstract 1
101710092149 Peptidyl-prolyl cis-trans isomerase-like 4 Proteins 0.000 abstract 1
101710113444 Probable parvulin-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 abstract 1
101710090737 Probable peptidyl-prolyl cis-trans isomerase Proteins 0.000 abstract 1
101710133309 Putative peptidyl-prolyl cis-trans isomerase Proteins 0.000 abstract 1
101710124237 Short-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 abstract 1
210000001185 bone marrow Anatomy 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
239000000243 solution Substances 0.000 description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
210000004027 cell Anatomy 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 23
201000010099 disease Diseases 0.000 description 22
238000000034 method Methods 0.000 description 20
238000012360 testing method Methods 0.000 description 20
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
239000002253 acid Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
229940079593 drug Drugs 0.000 description 12
239000010410 layer Substances 0.000 description 12
239000007788 liquid Substances 0.000 description 12
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230000035755 proliferation Effects 0.000 description 12
102000000588 Interleukin-2 Human genes 0.000 description 11
108010002350 Interleukin-2 Proteins 0.000 description 11
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PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 9
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210000001744 T-lymphocyte Anatomy 0.000 description 9
150000002148 esters Chemical class 0.000 description 9
101150041968 CDC13 gene Proteins 0.000 description 8
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
230000027455 binding Effects 0.000 description 8
229960001265 ciclosporin Drugs 0.000 description 8
229930182912 cyclosporin Natural products 0.000 description 8
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238000004458 analytical method Methods 0.000 description 7
ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 7
229960002930 sirolimus Drugs 0.000 description 7
QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 7
208000024891 symptom Diseases 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
238000004128 high performance liquid chromatography Methods 0.000 description 6
229960003444 immunosuppressant agent Drugs 0.000 description 6
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
210000003734 kidney Anatomy 0.000 description 6
238000002386 leaching Methods 0.000 description 6
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
235000018102 proteins Nutrition 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 5
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OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
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229910052939 potassium sulfate Inorganic materials 0.000 description 1
235000011151 potassium sulphates Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
208000011511 primary membranoproliferative glomerulonephritis Diseases 0.000 description 1
230000008569 process Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000008439 repair process Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000009666 routine test Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
235000006414 serbal de cazadores Nutrition 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
LFAGQMCIGQNPJG-UHFFFAOYSA-N silver cyanide Chemical compound [Ag+].N#[C-] LFAGQMCIGQNPJG-UHFFFAOYSA-N 0.000 description 1
229940098221 silver cyanide Drugs 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
235000013599 spices Nutrition 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000003637 steroidlike Effects 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000004575 stone Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000002641 tar oil Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
WPWXYQIMXTUMJB-UHFFFAOYSA-N tert-butyl 3-(aminomethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(CN)C1 WPWXYQIMXTUMJB-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
210000000115 thoracic cavity Anatomy 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
238000004448 titration Methods 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
238000012546 transfer Methods 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
239000006200 vaporizer Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000012795 verification Methods 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/56—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having carbon atoms of carboxamide groups bound to carbon atoms of carboxyl groups, e.g. oxamides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Transplantation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Furan Compounds (AREA)

TW080105466A 1990-07-02 1991-07-15 TW215055B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/547,814 US5192773A (en)	1990-07-02	1990-07-02	Immunosuppressive compounds

Publications (1)

Publication Number	Publication Date
TW215055B true TW215055B (de)	1993-10-21

Family

ID=24186237

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW080105466A TW215055B (de)	1990-07-02	1991-07-15

Country Status (15)

Country	Link
US (5)	US5192773A (de)
EP (1)	EP0537269B1 (de)
JP (2)	JP3095247B2 (de)
KR (1)	KR100197306B1 (de)
AT (1)	ATE159247T1 (de)
AU (2)	AU660623B2 (de)
BR (2)	BR1100732A (de)
CA (1)	CA2086428A1 (de)
DE (1)	DE69127970T2 (de)
DK (1)	DK0537269T3 (de)
ES (1)	ES2109269T3 (de)
GR (1)	GR3025918T3 (de)
SG (1)	SG49663A1 (de)
TW (1)	TW215055B (de)
WO (1)	WO1992000278A1 (de)

Families Citing this family (143)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5530101A (en)	1988-12-28	1996-06-25	Protein Design Labs, Inc.	Humanized immunoglobulins
US20040049014A1 (en) *	1988-12-28	2004-03-11	Protein Design Labs, Inc.	Humanized immunoglobulins
US5192773A (en) *	1990-07-02	1993-03-09	Vertex Pharmaceuticals, Inc.	Immunosuppressive compounds
US5723459A (en) *	1991-05-09	1998-03-03	Vertex Pharmaceuticals Incorporated	Biologically active acylated amino acid derivatives
DE69229782T2 (de) *	1991-05-09	2000-04-27	Vertex Pharmaceuticals Inc., Cambridge	Neue immunsuppressive verbindungen
US5620971A (en) *	1991-05-09	1997-04-15	Vertex Pharmaceuticals Incorporated	Biologically active acylated amino acid derivatives
MX9202466A (es) *	1991-05-24	1994-06-30	Vertex Pharma	Compuestos inmunosupresores novedosos.
CA2091194A1 (en) *	1992-04-08	1993-10-09	Richard D. Connell	2-oxo-ethyl derivatives as immunosuppressants
US5397703A (en) *	1992-07-09	1995-03-14	Cetus Oncology Corporation	Method for generation of antibodies to cell surface molecules
NZ314207A (en) *	1992-09-28	2000-12-22	Vertex Pharma	1-(2-Oxoacetyl)-piperidine-2-carboxylic acid derivatives as multi drug resistant cancer cell sensitizers
US5846981A (en) *	1993-05-28	1998-12-08	Gpi Nil Holdings Inc.	Inhibitors of rotamase enzyme activity
US5798355A (en) *	1995-06-07	1998-08-25	Gpi Nil Holdings, Inc.	Inhibitors of rotamase enzyme activity
US20020099067A1 (en) *	1993-07-08	2002-07-25	Ulrich Posanski	Pharmaceutical compositions for sparingly soluble therapeutic agents
ES2065290B1 (es) *	1993-07-29	1995-11-01	Consejo Superior Investigacion	Utilizacion de inhibidores enzimaticos para el tratamiento de enfermedades causadas por parasitos.
US6566386B2 (en)	1993-08-09	2003-05-20	Nippon Zoki Pharmaceutical Co., Ltd.	Immunomodulating and antiinflammatory agent
JP3193205B2 (ja) *	1993-08-09	2001-07-30	日本臓器製薬株式会社	好酸球増多抑制剤
US5453431A (en) *	1993-10-29	1995-09-26	Gilman; Andrew L.	Use of hydroxychloroquine for treatment of graft-versus-host disease
ATE149485T1 (de) *	1993-11-02	1997-03-15	Hoechst Ag	Substituierte heterocyclische carbonsäureamidester, ihre herstellung und ihre verwendung als arzneimittel
CA2138929A1 (en) *	1993-12-30	1995-07-01	Klaus Weidmann	Substituted heterocyclic carboxamides, their preparation and their use as pharmaceuticals
US5898029A (en) *	1994-04-12	1999-04-27	The John Hopkins University	Direct influences on nerve growth of agents that interact with immunophilins in combination with neurotrophic factors
US6150527A (en) *	1994-08-18	2000-11-21	Ariad Pharmaceuticals, Inc.	Synthetic multimerizing agents
US6133456A (en) *	1994-08-18	2000-10-17	Ariad Gene Therapeutics, Inc.	Synthetic multimerizing agents
US20030036654A1 (en)	1994-08-18	2003-02-20	Holt Dennis A.	Synthetic multimerizing agents
US6294383B1 (en)	1994-11-08	2001-09-25	The Mclean Hospital Corporation	Porcine neural cells and their use in treatment of neurological deficits due to neurodegenerative diseases
US6277372B1 (en)	1994-11-08	2001-08-21	Diacrin, Inc.	Porcine neural cells and their use in treatment of neurological deficits due to neurodegenerative diseases
US6204053B1 (en) *	1994-11-08	2001-03-20	Diacrin, Inc.	Porcine cortical cells and their use in treatment of neurological deficits due to neurodegenerative diseases
US5543423A (en) *	1994-11-16	1996-08-06	Vertex Pharmaceuticals, Incorporated	Amino acid derivatives with improved multi-drug resistance activity
US5726184A (en) *	1995-05-19	1998-03-10	Vertex Pharmaceuticals Incorporated	Tetralin compounds with improved MDR activity
US6291510B1 (en)	1995-06-07	2001-09-18	Gpi Nil Holdings, Inc.	Small molecule inhibitors of rotamase enzyme activity
US5614547A (en) *	1995-06-07	1997-03-25	Guilford Pharmaceuticals Inc.	Small molecule inhibitors of rotamase enzyme
AT500192B1 (de) *	1995-06-07	2008-05-15	Guilford Pharm Inc	Neurotrophe verbindung, diese enthaltende pharmazeutische masse, verwendung der verbindung und verfahren zu ihrer herstellung
US5696135A (en) *	1995-06-07	1997-12-09	Gpi Nil Holdings, Inc.	Inhibitors of rotamase enzyme activity effective at stimulating neuronal growth
AT500193B1 (de) *	1995-06-07	2007-11-15	Guilford Pharm Inc	Neurotrophe verbindung und verfahren zu ihrer herstellung
US5833987A (en) *	1995-06-07	1998-11-10	Trustees Of Dartmouth College	Treatment of T cell mediated autoimmune disorders
GB2332673A (en) *	1995-06-07	1999-06-30	Guilford Pharm Inc	Small molecule inhibitors of rotamase enzyme activity
US7056935B2 (en) *	1995-06-07	2006-06-06	Gpi Nil Holdings, Inc.	Rotamase enzyme activity inhibitors
US5859031A (en) *	1995-06-07	1999-01-12	Gpi Nil Holdings, Inc.	Small molecule inhibitors of rotamase enzyme activity
US6509477B1 (en)	1998-11-12	2003-01-21	Guilford Pharmaceuticals Inc.	Small molecule inhibitors of rotamase enzyme activity
US6037370A (en) *	1995-06-08	2000-03-14	Vertex Pharmaceuticals Incorporated	Methods and compositions for stimulating neurite growth
JPH0959180A (ja)	1995-08-11	1997-03-04	Nippon Zoki Pharmaceut Co Ltd	活性化免疫グロブリン
IL135495A (en) *	1995-09-28	2002-12-01	Hoechst Ag	Intermediate compounds for the preparation of quinoline-converted amines - 2 - carboxylic acid
US5801197A (en) *	1995-10-31	1998-09-01	Gpi Nil Holdings, Inc.	Rotamase enzyme activity inhibitors
JP3089350B2 (ja)	1995-11-20	2000-09-18	ギルフォードファーマシューティカルズインコーポレイテッド	シクロフィリンロタマーゼ活性の阻害剤
US5717092A (en) *	1996-03-29	1998-02-10	Vertex Pharmaceuticals Inc.	Compounds with improved multi-drug resistance activity
DE19616509A1 (de) *	1996-04-25	1998-01-15	Asta Medica Ag	Neue spezifische Immunophilin-Liganden als Antiasthmatika, Immunsuppressiva
US5786378A (en) *	1996-09-25	1998-07-28	Gpi Nil Holdings, Inc.	Heterocyclic thioesters
US5801187A (en) *	1996-09-25	1998-09-01	Gpi-Nil Holdings, Inc.	Heterocyclic esters and amides
US6218424B1 (en)	1996-09-25	2001-04-17	Gpi Nil Holdings, Inc.	Heterocyclic ketone and thioester compounds and uses
US5811434A (en) *	1996-11-13	1998-09-22	Vertex Pharmacueticals Incorporated	Methods and compositions for stimulating neurite growth
US5780484A (en) *	1996-11-13	1998-07-14	Vertex Pharmaceuticals Incorporated	Methods for stimulating neurite growth with piperidine compounds
EP0959882A4 (de) *	1996-12-31	2001-12-05		N-gebundene harnstoffe und carbamate von heterocyclischen thioestern
JP2002515051A (ja) *	1996-12-31	2002-05-21	ジーピーアイエヌアイエルホールディングスインコーポレイテッド	ヘテロ環式チオエステルのｎ−結合スルホンアミド
US5874449A (en) *	1996-12-31	1999-02-23	Gpi Nil Holdings, Inc.	N-linked sulfonamides of heterocyclic thioesters
US5935989A (en) *	1996-12-31	1999-08-10	Gpi Nil Holdings Inc.	N-linked ureas and carbamates of heterocyclic thioesters
JPH10212246A (ja)	1997-01-30	1998-08-11	Nippon Zoki Pharmaceut Co Ltd	経口投与用製剤
US5846979A (en) *	1997-02-28	1998-12-08	Gpi Nil Holdings, Inc.	N-oxides of heterocyclic esters, amides, thioesters, and ketones
US6271244B1 (en)	1998-06-03	2001-08-07	Gpi Nil Holdings, Inc.	N-linked urea or carbamate of heterocyclic thioester hair growth compositions and uses
US20010049381A1 (en) *	1997-06-04	2001-12-06	Gpl Nil Holdings, Inc.,	Pyrrolidine derivative hair growth compositions and uses
US6187784B1 (en)	1998-06-03	2001-02-13	Gpi Nil Holdings, Inc.	Pipecolic acid derivative hair growth compositions and uses
US5945441A (en) *	1997-06-04	1999-08-31	Gpi Nil Holdings, Inc.	Pyrrolidine carboxylate hair revitalizing agents
US6187796B1 (en)	1998-06-03	2001-02-13	Gpi Nil Holdings, Inc.	Sulfone hair growth compositions and uses
US6274602B1 (en) *	1998-06-03	2001-08-14	Gpi Nil Holdings, Inc.	Heterocyclic thioester and ketone hair growth compositions and uses
US6852496B1 (en) *	1997-08-12	2005-02-08	Oregon Health And Science University	Methods of screening for agents that promote nerve cell growth
DE19742263A1 (de) *	1997-09-25	1999-04-01	Asta Medica Ag	Neue spezifische Immunophilin-Liganden als Antiasthmatika, Antiallergika, Antirheumatika, Immunsuppressiva, Antipsoriatika, Neuroprotektiva
US5968921A (en)	1997-10-24	1999-10-19	Orgegon Health Sciences University	Compositions and methods for promoting nerve regeneration
JP2002516857A (ja)	1998-06-02	2002-06-11	ブリストルーマイヤーズスクイブカンパニー	神経栄養性ジフルオロアミド剤
WO1999062513A1 (en) *	1998-06-03	1999-12-09	Merck & Co., Inc.	Hiv integrase inhibitors
HUP0102935A3 (en)	1998-06-03	2002-01-28	Gpi Nil Holdings Inc Wilmingto	N-linked sulfonamides of n-heterocyclic carboxylic acids or carboxylic acid isosteres and pharmaceutical compositions containing them
CN100351230C (zh) *	1998-06-03	2007-11-28	Gpinil控股公司	N－杂环化合物的羧酸和羧酸电子等排物
US6262055B1 (en)	1998-06-03	2001-07-17	Merck & Co., Inc.	HIV integrase inhibitors
EP1085853A1 (de) *	1998-06-03	2001-03-28	GPI NIL Holdings, Inc.	Haarwuchszusammensetzungen basiernd auf heterozyklischem ester und amid und anwendungen
US6429215B1 (en)	1998-06-03	2002-08-06	Gpi Nil Holdings, Inc.	N-oxide of heterocyclic ester, amide, thioester, or ketone hair growth compositions and uses
HUP0102532A3 (en) *	1998-06-03	2002-06-28	Gpi Nil Holdings Inc Wilmingto	Aza-heterocyclic compounds used to treat neurological disorders and hair loss and process for their preparation and pharmaceutical compositions containing them
US6306891B1 (en)	1998-06-03	2001-10-23	Merck & Co., Inc.	HIV integrase inhibitors
US6380249B1 (en)	1998-06-03	2002-04-30	Merck & Co., Inc.	HIV integrase inhibitors
US6172087B1 (en)	1998-06-03	2001-01-09	Gpi Nil Holding, Inc.	N-oxide of heterocyclic ester, amide, thioester, or ketone hair growth compositions and uses
EP1842845B1 (de) *	1998-06-03	2014-07-16	GliaMed, Inc.	Azaheterozyklischederivate zur behandlung von haarausfall und neurologischer krankheiten
ZA9811063B (en) *	1998-06-03	2000-07-07	Guilford Pharm Inc	Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds.
US6331537B1 (en)	1998-06-03	2001-12-18	Gpi Nil Holdings, Inc.	Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds
PL345598A1 (en)	1998-07-17	2001-12-17	Agouron Pharma	Compounds, compositions, and methods for stimulating neuronal growth and elongation
GB9816358D0 (en) *	1998-07-27	1998-09-23	Angeletti P Ist Richerche Bio	Enzyme inhibitors
CA2338490A1 (en)	1998-07-27	2000-02-10	Sergio Altamura	Diketoacid-derivatives as inhibitors of polymerases
US6506788B1 (en)	1998-08-14	2003-01-14	Gpi Nil Holdings, Inc.	N-linked urea or carbamate of heterocyclic thioesters for vision and memory disorders
US7338976B1 (en) *	1998-08-14	2008-03-04	Gpi Nil Holdings, Inc.	Heterocyclic esters or amides for vision and memory disorders
US6339101B1 (en)	1998-08-14	2002-01-15	Gpi Nil Holdings, Inc.	N-linked sulfonamides of N-heterocyclic carboxylic acids or isosteres for vision and memory disorders
US6376517B1 (en) *	1998-08-14	2002-04-23	Gpi Nil Holdings, Inc.	Pipecolic acid derivatives for vision and memory disorders
US6333340B1 (en)	1998-08-14	2001-12-25	Gpi Nil Holdings, Inc.	Small molecule sulfonamides for vision and memory disorders
US6337340B1 (en)	1998-08-14	2002-01-08	Gpi Nil Holdings, Inc.	Carboxylic acids and isosteres of heterocyclic ring compounds having multiple heteroatoms for vision and memory disorders
JP4503180B2 (ja) *	1998-08-14	2010-07-14	ジーピーアイニルホールディングスインコーポレイテッド	視覚および記憶障害のための組成物および使用法
US6384056B1 (en)	1998-08-14	2002-05-07	Gpi Nil Holdings, Inc.	Heterocyclic thioesters or ketones for vision and memory disorders
US6395758B1 (en)	1998-08-14	2002-05-28	Gpi Nil Holdings, Inc.	Small molecule carbamates or ureas for vision and memory disorders
US7410995B1 (en)	1998-08-14	2008-08-12	Gpi Nil Holdings Inc.	N-linked sulfonamide of heterocyclic thioesters for vision and memory disorders
US6218423B1 (en)	1998-08-14	2001-04-17	Gpi Nil Holdings, Inc.	Pyrrolidine derivatives for vision and memory disorders
US7265150B1 (en)	1998-08-14	2007-09-04	Gpi Nil Holdings Inc.	Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds for vision and memory disorders
US6399648B1 (en)	1998-08-14	2002-06-04	Gpi Nil Holdings, Inc.	N-oxides of heterocyclic ester, amide, thioester, or ketone for vision and memory disorders
US6335348B1 (en)	1998-08-14	2002-01-01	Gpi Nil Holdings, Inc.	Nitrogen-containing linear and azepinyl/ compositions and uses for vision and memory disorders
US6462072B1 (en) *	1998-09-21	2002-10-08	Gpi Nil Holdings, Inc.	Cyclic ester or amide derivatives
US6307049B1 (en)	1998-09-30	2001-10-23	The Procter & Gamble Co.	Heterocyclic 2-substituted ketoamides
US6444205B2 (en)	1998-09-30	2002-09-03	Diacrin, Inc.	Transplantation of neural cells for the treatment of chronic pain or spasticity
US6300341B1 (en)	1998-09-30	2001-10-09	The Procter & Gamble Co.	2-substituted heterocyclic sulfonamides
US6228872B1 (en)	1998-11-12	2001-05-08	Bristol-Myers Squibb Company	Neurotrophic diamide and carbamate agents
JP2000143536A (ja)	1998-11-13	2000-05-23	Nippon Zoki Pharmaceut Co Ltd	抗浮腫剤
BR9916583A (pt) *	1998-12-25	2001-09-25	Shionogi & Co	Derivados heteroaromáticos tendo uma atividade inibitória contra integrase de hiv
US20020006901A1 (en) *	1999-02-05	2002-01-17	Aldo T. Iacono	Use of aerosolized cyclosporine for prevention and treatment of pulmonary disease
US6734211B1 (en)	1999-07-09	2004-05-11	Oregon Health & Sciences University	Compositions and methods for promoting nerve regeneration
WO2001017953A1 (en) *	1999-09-08	2001-03-15	Guilford Pharmaceuticals Inc.	Non-peptidic cyclophilin binding compounds and their use
AU1254101A (en) *	1999-09-20	2001-04-24	Charlotte-Mecklenburg Hospital Authority	Solution for the preservation of hearts
US6417189B1 (en)	1999-11-12	2002-07-09	Gpi Nil Holdings, Inc.	AZA compounds, pharmaceutical compositions and methods of use
US7253169B2 (en)	1999-11-12	2007-08-07	Gliamed, Inc.	Aza compounds, pharmaceutical compositions and methods of use
GT200000203A (es)	1999-12-01	2002-05-24		Compuestos, composiciones y metodos para estimular el crecimiento y elongacion de neuronas.
US6818643B1 (en)	1999-12-08	2004-11-16	Bristol-Myers Squibb Company	Neurotrophic bicyclic diamides
EP1242086B1 (de) *	1999-12-21	2005-10-05	AstraZeneca AB	Cd45 hemmer
EP1242363B1 (de) *	1999-12-21	2005-11-02	AstraZeneca AB	Cd45 inhibitoren
WO2001046195A1 (en)	1999-12-21	2001-06-28	Gpi Nil Holdings, Inc.	Hydantoin derivative compounds, pharmaceutical compositions, and methods of using same
EP1125925A1 (de) *	2000-02-15	2001-08-22	Applied Research Systems ARS Holding N.V.	Amin-Derivate zur Behandlung von Apoptosis
US7288551B1 (en)	2000-09-19	2007-10-30	Charlotte-Mecklenburg Hospital Authority	Solution for the preservation of hearts
MXPA03006666A (es)	2001-01-25	2004-05-31	Guilford Pharm Inc	Compuestos de union de ciclofilina carbociclicos trisubstituidos y su uso.
US6593362B2 (en)	2001-05-21	2003-07-15	Guilford Pharmaceuticals Inc.	Non-peptidic cyclophilin binding compounds and their use
WO2002096420A2 (en) *	2001-05-29	2002-12-05	Guilford Pharmaceuticals Inc.	Method for treating nerve injury caused by surgery
CA2450073C (en)	2001-07-25	2017-08-29	Biomarin Pharmaceutical Inc.	Compositions and methods for modulating blood-brain barrier transport
WO2003062773A1 (en) *	2002-01-24	2003-07-31	Pei Electronics, Inc.	Compact integrated infrared scene projector
WO2003105697A1 (en) *	2002-06-14	2003-12-24	Loma Linda University Medical Center	Vascular wound closure device and method
SI1539157T1 (sl) *	2002-09-18	2013-11-29	Trustees Of The University Of Pennsylvania	Rapamicin za uporabo pri inhibiciji ali preprečevanju horoidalne neovaskularizacije
JP2007505932A (ja) *	2003-09-18	2007-03-15	マクサイト，インコーポレイテッド	経強膜送達
EP1768662A2 (de)	2004-06-24	2007-04-04	Novartis Vaccines and Diagnostics, Inc.	Immunstimulatoren kleiner moleküle und assays für deren nachweis
US20060189551A1 (en) *	2004-10-04	2006-08-24	Duke University	Combination therapies for fungal pathogens
US20060194829A1 (en) *	2004-12-20	2006-08-31	Clackson Timothy P	Therapeutic materials and methods
CA2597590A1 (en)	2005-02-09	2006-08-17	Macusight, Inc.	Formulations for ocular treatment
US8663639B2 (en) *	2005-02-09	2014-03-04	Santen Pharmaceutical Co., Ltd.	Formulations for treating ocular diseases and conditions
EP2671508B1 (de)	2005-04-28	2020-09-16	Proteus Digital Health, Inc.	Pharma-Informatiksystem
KR101478164B1 (ko)	2006-02-09	2014-12-31	산텐 세이야꾸 가부시키가이샤	안정한 제제와 그 제조 및 사용 방법
AU2007230964B2 (en)	2006-03-23	2012-07-19	Santen Pharmaceutical Co., Ltd.	Formulations and methods for vascular permeability-related diseases or conditions
US7943775B2 (en) *	2006-06-21	2011-05-17	The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services	Small molecules for imaging protein-protein interactions
JP2010503710A (ja)	2006-09-18	2010-02-04	ラプトールファーマシューティカルインコーポレイテッド	受容体関連タンパク質（ｒａｐ）結合体の投与による肝障害の処置
US20080306098A1 (en) *	2006-11-06	2008-12-11	Mutz Mitchell W	Pharmacokinetics of protease inhibitors and other drugs
US20080265343A1 (en) *	2007-04-26	2008-10-30	International Business Machines Corporation	Field effect transistor with inverted t shaped gate electrode and methods for fabrication thereof
US20090054334A1 (en) *	2007-05-23	2009-02-26	Mutz Mitchell W	Combinatorial improvement of bifunctional drug properties
US20090053245A1 (en) *	2007-05-29	2009-02-26	Mutz Mitchell W	Pharmacokinetics and Efficacy of Anti-Angiogenic Drugs and Drugs Treating Diseases of the Blood
US20100284993A1 (en) *	2007-10-24	2010-11-11	Mutz Mitchell W	Enhancing the Efficacy of Anti-Infective Therapeutics
KR20180114970A (ko)	2009-05-06	2018-10-19	라보라토리 스킨 케어, 인크.	활성제-칼슘 포스페이트 입자 복합체를 포함하는 피부 전달 조성물 및 이들을 이용하는 방법
US20110065723A1 (en)	2009-09-11	2011-03-17	Vertex Pharmaceuticals Incorporated	Compositions of n-benzyl-3-(4-chlorophenyl)-2-[methyl-[2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl]amino]-n-[3-(4-pyridyl)-1-[2-(4-pyridyl)ethyl]propyl]propanamide and uses thereof
US20120077778A1 (en)	2010-09-29	2012-03-29	Andrea Bourdelais	Ladder-Frame Polyether Conjugates
EP2705856A1 (de)	2012-09-07	2014-03-12	Deutsches Zentrum für Neurodegenerative Erkrankungen e.V.	Verbindungen zur Behandlung von neurodegenerativen Erkrankungen

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3646061A (en) *	1968-06-10	1972-02-29	Ajinomoto Kk	Method of preparing n-alkoxalyl and n-formyl derivatives of alpha-amino acid esters
DE2328391A1 (de) *	1972-06-19	1974-01-10	Degussa	Trialkoxycinnamoylaminocarbonsaeuren
CN86101850A (zh) *	1985-03-22	1987-02-04	森得克斯(美国)有限公司	N，n′-二烷基胍基二肽的制造方法与用途
DE4015255A1 (de) *	1990-05-12	1991-11-14	Hoechst Ag	Oxalyl-aminosaeurederivate, verfahren zu ihrer herstellung und ihrer verwendung als arzneimittel zur inhibierung der prolyl-hydroxylase
US5192773A (en) *	1990-07-02	1993-03-09	Vertex Pharmaceuticals, Inc.	Immunosuppressive compounds

1990
- 1990-07-02 US US07/547,814 patent/US5192773A/en not_active Expired - Lifetime
1991
- 1991-07-02 US US07/724,734 patent/US5330993A/en not_active Expired - Lifetime
- 1991-07-02 EP EP91913236A patent/EP0537269B1/de not_active Revoked
- 1991-07-02 CA CA002086428A patent/CA2086428A1/en not_active Abandoned
- 1991-07-02 AU AU82855/91A patent/AU660623B2/en not_active Ceased
- 1991-07-02 KR KR1019920703413A patent/KR100197306B1/ko not_active Expired - Fee Related
- 1991-07-02 SG SG1996003267A patent/SG49663A1/en unknown
- 1991-07-02 DK DK91913236.5T patent/DK0537269T3/da active
- 1991-07-02 ES ES91913236T patent/ES2109269T3/es not_active Expired - Lifetime
- 1991-07-02 JP JP03512655A patent/JP3095247B2/ja not_active Expired - Lifetime
- 1991-07-02 DE DE69127970T patent/DE69127970T2/de not_active Revoked
- 1991-07-02 WO PCT/US1991/004694 patent/WO1992000278A1/en not_active Ceased
- 1991-07-02 AT AT91913236T patent/ATE159247T1/de not_active IP Right Cessation
- 1991-07-15 TW TW080105466A patent/TW215055B/zh active
1993
- 1993-03-08 US US08/027,870 patent/US5665774A/en not_active Expired - Lifetime
1994
- 1994-04-11 US US08/226,011 patent/US5516797A/en not_active Expired - Lifetime
1995
- 1995-06-01 US US08/456,572 patent/US5622970A/en not_active Expired - Lifetime
- 1995-10-06 AU AU33093/95A patent/AU692915B2/en not_active Ceased
1997
- 1997-05-09 BR BR1100732-0A patent/BR1100732A/pt active IP Right Grant
- 1997-05-12 BR BR1100764-8A patent/BR1100764A/pt active IP Right Grant
1998
- 1998-01-15 GR GR980400088T patent/GR3025918T3/el unknown
1999
- 1999-11-25 JP JP33498999A patent/JP3360054B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JP3360054B2 (ja)	2002-12-24
WO1992000278A1 (en)	1992-01-09
DK0537269T3 (da)	1998-06-02
KR100197306B1 (ko)	1999-06-15
KR930701403A (ko)	1993-06-11
HK1004066A1 (en)	1998-11-13
AU660623B2 (en)	1995-07-06
AU692915B2 (en)	1998-06-18
DE69127970T2 (de)	1998-03-05
AU3309395A (en)	1996-01-11
ES2109269T3 (es)	1998-01-16
GR3025918T3 (en)	1998-04-30
BR1100764A (pt)	2000-02-08
DE69127970D1 (de)	1997-11-20
JPH06501457A (ja)	1994-02-17
US5330993A (en)	1994-07-19
ATE159247T1 (de)	1997-11-15
US5665774A (en)	1997-09-09
EP0537269A1 (de)	1993-04-21
JP3095247B2 (ja)	2000-10-03
AU8285591A (en)	1992-01-23
US5622970A (en)	1997-04-22
CA2086428A1 (en)	1992-01-03
BR1100732A (pt)	2000-06-06
US5516797A (en)	1996-05-14
JP2000143599A (ja)	2000-05-23
US5192773A (en)	1993-03-09
EP0537269B1 (de)	1997-10-15
SG49663A1 (en)	1998-06-15

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